My Midlife Awaening

After things ended with Matt Jodi talked me into going on vacation with her to what she calls her special place. Since I met with Jodi she goes to this resort about 3 times a year to relax and enjoy. She has asked me to go a couple of times since I met her but I never took her up on it until now.

Jodi made all the plans as we arrived on a Friday afternoon at this high-class resort. Jodi filled me in ahead of time that there were mostly couples there but always opportunities to hook up that she would show me, plus she would be taking us on a fun outing on Sunday.

That Friday night we had a blast most people go from Sat to Sat so it was the last night for the majority of the guests and Jodi knew this and we were having drinks and hanging out. I learned something about Jodi that night when she went back to a room with a couple, I did not know she was bi. I on the other hand hooked up with a guy who I took back to my room for a quickie whose wife was asleep already and they were leaving the next day.

The next day Saturday we lounged at the resort all day relaxing and showing off our bodies in bikinis that we worked hard to stay in shape for, and also looking at the new people coming in for the week. That night we flirted around with some people having drinks and lining up what could be a good week.

Sunday we got up early as Jodi has a special day planned at a different resort that she said she goes to every time. A bus took us there and Jodi explained that what happens here stays here between us, she rented a private cabana and sets it up ahead of time with the guy who runs it and takes care of her for the day, said with a wink. She said you can join in or watch your call, how much you want to do, I was unsure what was all going to happen.

We arrived at the resort and checked and took a walk to the private cabana, as we approached I heard someone say Ms. Jodi welcome back, and this guy came over and greeted us, and asked Jodi who I was. Jodi introduce me and he introduced himself as Willy who would be taking care of us today. He then guided us to our cabana, it sat up on a hillside very nice and big with a deck and built-in hot tub for two in the front and a section in the back with couches and air conditioner and private from anyone seeing.

Once inside Willy said to Jodi that everything is set up and would Ms. Lesley be getting the same treatment, Jodi looked at me and said that's up to her if she wants to. With that, Jodi sat down on the couch motioning Willy over, and as he stood in front of her she pulled his shorts down and took his cock in her mouth. No Willy I would guess is about 6 feet tall thin, black, with the biggest cock I ever saw, and here I was watching my friend suck it like a porn star. After a couple of minutes, he pulled it out not coming, and said he would be back, has to get others set up, but he will be back soon. He said Freddy and some other guy's name I forget are on today, which made Jodi happy. Once he left I looked at Jodi and said what the fuck and she said this is her day she enjoys being a true slut, happened a couple of years ago and each time she comes back she hooks up with Willy and he has others in to join. She said you are more than welcome to join, watch, or just lay on the deck while they are back here.

That day I watched my friend be a true slut there were three guys who took turns coming to the cabana all-day to get sucked, and fuck Jodi. At one point two guys were in there as I watched her suck one and fuck another. later in the day and after some drinks I finally joined and blew Willy, I think it was more that I wanted his huge cock, and was curious about being with a black man. I did my best to suck his monster, but I was not as good as Jodi and after sucking him for 5 minutes he fucked her one final time.

It was a hot scene but it wasn't for me, I got off more on watching Jodi, afterwards, we headed back to our resort. That Sunday night Jodi was hanging with a couple, she told me later they were looking for a female to join, they didn't hook up that night because Jodi said she was sore from the day's events but this would be her go-to for the rest of the week. I did hook up with a guy who was married similar to my first night, his wife was in bed already, so he joined me for a quickie in my room.

The next day Monday we relaxed all day I saw the guy from the night before with his wife, she was hot, and he and I gave each other looks throughout the day. Jodi and the couple hooked up during the day and at night, and I hooked up with that guy again later that night like the previous night, it felt so wrong but so good at the same time.

The day Tuesday Jodi had planned a Spa day for us for all afternoon that was part of the resort, it was amazing being pampered having all the treatments, and the final step was a massage, a massage that would change me forever.

We were escorted to the spa room where we met our masseuse, The one knew Jodi from the past and introduced herself to me, I remember it like it was yesterday, she was of Filipino descent and her name was Darna. She was very attractive, and found out later she was 30. As Darna and Jodi made small talk for a minute catching up Jodi said please take care of my friend referring to me, and then told her something in private before she walked away with her masseuse, and Darna escorted me to our room.

Once in the room she dimmed the lights and brought me over to the table, I only had on a robe from my early spa treatments and took it off and laid on my stomach on the table. I have had massages in the past, but this one was different it felt amazing, not sure if it was because I was so relaxed being on vacation or spending the last couple hours at the spa, but I was on cloud 9. I was enjoying the best massage of my life fully relaxed until I felt her hands working on my inner thighs getting very close to my area. I didn't say anything at 1st as I lay there thinking, I have never had a woman touch me or thought of it, but here I was feeling myself getting wet with this strange woman teasing me. Finally, I felt her fingers touch my pussy and I must have jumped a little and said what are you doing. I was still on my stomach as she calmed me in a nice soft voice and said Ms. Jodi said to take care of you that you have never been touched by a woman, something I confessed to Jodi when she told me she was bi, Darna just said relax, enjoy and let me take care of you. I never said anything, but my body language accepted it and she knew it. As I lay there this woman rubbed my inner thighs, teasing me, making me wet like never before, while she occasionally rubbed my pussy causing me to moan.

After a bit of that, she had me turn over on my back, I was lying there naked as Darna rubbed me all over. She kept it non-sexual rubbing my arms, shoulders, and legs at first. As much as I was horny and wet I was nervous and had my legs together. She finally started to tease me, rubbing my nipples, making me moan, and working her way to my legs. She talked again saying trust her, as she tried to work my legs apart, and I finally gave in and spread my legs for her. From there I don't recall everything that she did, she teased me rubbing my inner legs, kept rubbing my nipples and finally she started to finger me. This was not like a man, she was so soft and gentle, taking her time, but I came quickly and at that point, I had the best orgasm of my life.

She kept rubbing me all over bringing me down from the high of the most amazing orgasm of my life and then helped me up saying our time was done. I was on such a high I don't recall saying anything, she helped me put my robe on. But before leaving she said the spa offers private massages in the room If I was interested and she believes she has openings this week, and if I wanted she can take me to the receptionist to sign up. I finally talked and said that could be nice, as she showed me out before she opened the door she said thank you for letting me massage you as she kissed me on my mouth, I opened my mouth accepting her tongue another first which lasted maybe 10 seconds.

Darna guided me out of the room to the sitting area I was at before meeting her and said wait here, and 2 minutes later returned with another girl, Darna said Ms. Lesley is interested in an in-room massage, Darna then shook my hand and left. The lady then said the massages in rooms are 50 or 100 minutes, and the masseuse brings the table, and most people like it set up on their balcony. She then asked did I like Darna or want to try someone else, I said Darna was good let's stay with her. She then said she only had 50 minutes this week and her next available was tomorrow night Wednesday at 5, she then showed me the price which was fine and would be billed to the room.

I then went back to get dressed and met with Jodi who had a grin on her face and asked how my massage was, I gave her a look as we went back telling her, thank you for that. We dressed and met for a dinner at the bar as I told her what happened along with making an in-room appointment the next day. I said to Jodi I hope I get the same type of massage, to which Jodi laughed and said honey if she recommended the in-room massage to you she doesn't want to give you a massage, but she wants to have sex with you. I must have been shocked and said are you serious and Jodi said well it's how we hooked up at first. At this point Jodi excused herself and joined the couple she was seeing, I on the other hand could not get Darna out of my mind and now thinking about the next day and seeing her.

I blew off that guy that night and had drinks going back to my room, and for the first time in my life, I masturbated to a woman, Daran of course. The next day I hung out relaxing and thinking about what would happen when I met Darna at 5, I saw Jodi a little but she was fully hanging with the couple having fun. Later in the afternoon, I headed back to my room, showering and preparing for my so-called massage, not sure what to wear I settled on a robe.

I must have sat there from 4:30 till 5 looking at the door and nervous, but also wet at the same time. At 5 sharp there was a knock on the door, and I got even more nervous, I opened the door, and there she was this sexy woman who, just 24 hours earlier, given me the best orgasm of my life and then kissed me. She came in and put the table down as the door closed, she then turned to me and said she was happy I booked this. I am not sure what got into me, but my nervousness went away and I kissed her as she kissed me the previous day. It was very passionate as she pulled the belt loose from my robe, letting it drop as we made our way to my bed. as I lay on my back she pulled her clothes off and I got to see her naked for the first time. Her body was incredible, her nipples were like little erasers, she then lay on me as we kissed more. After a couple more minutes, she broke the kiss as she moved down spreading my legs and tasting me, performing oral the best ever I had up until that moment, I came fast from her mouth.

I then told her I wanted to taste her, so we swapped positions as she guided me to her pussy, and I had my first taste ever of pussy and she was so sweet. She guided me knowing it was my 1st time, and I was able to bring her to orgasm. After she came we lay there kissing, and rubbing each other both of us still horny, leading to us 69 which was very hot for me, and then she broke it and guided us to something else new for me, which I learned later was called, tribbing, which felt amazing bringing us both to orgasm again. She had to go as the time was up, I asked her can she stay but she said that it was impossible if she got caught she would be fired, she dressed and we had one more passionate kiss and she left.

I lay in bed and fell asleep for about an hour, woke up thru on a dress, and didn't shower since I wanted to smell like her. I did not see Jodi, and again I blew the guy off, I lost interest and was only thinking of Darna. The next day Thursday I stopped by the spa I wanted another in-room massage with Darna they told me she was booked all week, but the girl who helped me the other day came over and helped me say she could move an appointment around with someone who didn't request Darna since I was booking again this week. I asked for 100 minutes but they said she only had 50 again, they were able to fit me in late Friday but mentioned it was her last appointment for the day so if she was interested in working late she might be able to do the 100, they would let me know.

I saw Jodi and filled her in she laughed and said she created a monster, again the rest of Thursday I didn't hook up with anyone as I just thought about Darna. Friday I just relaxed waiting for my so-called appointment. When I went back to my room on Friday I had a message that they could accommodate the 100-minute massage. At 5 sharp there was a knock again, I opened the door naked letting in Darna, and as soon as she put her table down that she had to bring we were all over each other.

I pulled her clothes off and we made our way to the bed, we took our time and performed oral on each other using our fingers teasing each other. We 69, tribbed, kissed a lot and had multiple orgasams in that time together, we kissed one final time for a couple of minutes saying goodbye.

That night I sat at the bar having a couple of drinks thinking about my week and what was next. The next morning Jodi and I left, and I didn't say that much, I so enjoyed my time with Darna, and thought was I now Bi, would I want a woman when I got back home. Regardless it was a great vacation, when we got home I thanked Jodi for showing me a different path.

My story will continue as I figure out if I am now a lesbian.